TY - JOUR AU - Liu, Jiangguang; Yan, Jiajie; Qin, Dongguang; Cai, Qian TI - An Unexpected Inversion of Enantioselectivity in a Copper-Catalyzed Intramolecular­ Desymmetric Aryl C–N Coupling Reaction SN - 0039-7881 SN - 1437-210X PY - 2014 JO - Synthesis JF - Synthesis LA - EN VL - 46 IS - 14 SP - 1917 EP - 1923 ET - 2014/05/09 DA - 2014/07/07 KW - asymmetric desymmetrization KW - indolines KW - copper catalysis KW - N-arylation KW - inversion AB - Enantioselective formation of indolines was achieved through desymmetrization of α,α-bis(2-iodobenzyl)glycines under the catalysis of copper(I) iodide and (2S,3aS,7aS)-octahydro-1H-­indole-2-carboxylic acid. An unexpected inversion of enantioselectivity was observed when achiral additives such as 4-(N,N-dimethylamino)pyridine were added which work together with the ligand. The configuration-reversed products were obtained in moderate yields as well as moderate ee values. PB - © Georg Thieme Verlag DO - 10.1055/s-0033-1338638 UR - http://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0033-1338638 ER -